This project will explore the ability of chemical additives to direct the formation of products in alkene ozonolysis, one of the most important oxidative transformations in organic chemistry. While the central role of carbonyl oxides in alkene ozonolysis has been known for more than a half century, the scope of reagents able to react with these short-lived intermediates remains extremely limited. The hypothesis central to the research is that the presence of specific additives will control the reactivity of the intermediate carbonyl oxides to favor formation of particular products, some of which are completely unavailable by traditional methodology. The project will focus on three areas: First, the generation and fragmentation of carbonyl oxide-derived zwitterions will be investigated as a new approach for "reductive" ozonolysis, a process which directly produces carbonyl products without the need for a separate reductive step. Second, ozonolysis in the presence of Lewis acids will be explored as a means for enhancing nucleophilic trapping of carbonyl oxides. Finally, generation and fragmentation of heteroozonides will be explored for the direct conversion of alkenes to carboxyl groups.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Patrick Dussault at the Department of Chemistry at the University of Nebraska-Lincoln. Professor Dussault's research efforts revolve around new methods for organic oxidations with ozone, an environmentally sustainable oxidant generated from oxygen and electricity. The anticipated outcome of the research, expanded applications of alkene ozonolysis in organic synthesis, will have a positive impact on the pharmaceutical and agricultural industries. The award will also support theoretical investigations of carbonyl oxide reactivity in the laboratories of a co-investigator, Professor Keith Kuwata of Macalester College.
